Six Figure Work

VP, Regional Underwriting Manager Midwest (Core Middle Market)

CNA

Company websitecna.com (CNA, opens in new tab)

Base salary $194K  to $308K

Employer-published annual base salary, USD. Advertised base range in Chicago, IL

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  • LocationChicago, IL
  • WorkplaceWorkplace not stated
  • Status at last checkSource accepting applications when checked
  • Last checked (1 h ago) · observed since

About this job

You have a clear vision of where your career can go. And we have the leadership to help you get there. At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential. 

CNA is looking for a strategic and experienced underwriting leader to lead and grow our Core Middle Market business in the Midwest region. As the Regional Underwriting Manager, you will develop underwriting talent, drive underwriting excellence, strengthening portfolio performance across multiple products, and deliver sustainable, profitable growth across the region. This highly visible leadership role offers the opportunity to shape business strategy, build trusted partnerships, and make a meaningful impact within an organization that values leadership, accountability, and long-term success.

JOB DESCRIPTION:

Essential Duties & Responsibilities

Performs a combination of duties in accordance with departmental guidelines:

  • The VP, Regional Underwriting Manager has full accountability and ownership for underwriting and for achieving production and profitability goals for an assigned region and aligns with top distribution firms to promote profitable growth opportunities.

  • This position works within their delegated underwriting authority and guidelines to drive underwriting, operational and transactional excellence throughout the underwriting chain and across their region.

  • Delegates authority to subordinate underwriters and partners with the enterprise Property and Casualty groups to govern referral thresholds, underwriting authority and establish clear paths of accountability and ownership throughout their respective hierarchy.

  • This role will partner with the SVP and VP level sales and production leaders within their territory to maximize profitable growth opportunities with agents & brokers.

  • Leads, directs and has full management accountability for staff in area of responsibility with an emphasis on talent management, succession planning and skill development in accordance with strategic direction.

  • This leader will have direct ownership of all aspects of underwriter performance and accountability to promote a high performing culture into their respective regions.

  • Drives implementation of strategic and operational objectives with significant impact on the short-term success of multiple products within a geographic region.

  • Analyzes underwriting performance based on quarterly regional evaluations of profit, production, rate, retention, agency performance and cross-sell opportunities. Provides results to members of the management team and develops plans to resolve issues.

May perform additional duties as assigned.
 

Reporting Relationship

Typically SVP or above

Skills, Knowledge & Abilities


1. Mastery of underwriting discipline and knowledge in the insurance field and a broad understanding of the critical issues in other related areas.
2. Advanced communication skills which are critical to building consensus across area of influence (external and/or internal relationships), teams and/or matrix environment.
3. Strong leadership and management skills demonstrating integrity and professionalism.
4. Ability to drive results by identifying and resolving significant problems within scope of responsibility.
5. Senior level knowledge of the insurance industry, its products and services.
6. Knowledge of Microsoft Office 365 and other business-related software.
7. Strong knowledge of assigned business line and insurance industry.
 

Education & Experience

1. Bachelor’s degree with Master’s preferred in a related discipline, or equivalent.
2. Typically a minimum of 12 years of related work experience, with seven years management experience. 
3. Chartered Property Casualty Underwriter (CPCU) designation preferred.

In certain jurisdictions, CNA is legally required to include a reasonable estimate of the compensation for this role. In District of Columbia, California, Colorado, Connecticut, Illinois, Maryland, Massachusetts, New York and Washington, the national base pay range for this job level is $194,000 to $308,000 annually. Salary determinations are based on various factors, including but not limited to, relevant work experience, skills, certifications and location. CNA offers a comprehensive and competitive benefits package to help our employees – and their family members – achieve their physical, financial, emotional and social wellbeing goals.  For a detailed look at CNA’s benefits, please visit cnabenefits.com.


CNA utilizes AI-enabled technology during the recruiting process. For more information, please visit our careers page.


CNA is committed to providing reasonable accommodations to qualified individuals with disabilities in the recruitment process. To request an accommodation, please contact [email protected]

Source: CNA on Workday · View original posting (opens in new tab)

Pay in context

This role's base floor ($194,000) is above 93% of the 223 Finance & Accounting roles in Illinois listed on this site. Their median floor is $125,000; the middle half runs from $110,000 to $150,900.

Only jobs on this site count, and each one publishes a base salary of $100,000 or more, so this compares six-figure jobs with each other, not with the whole market. Computed Nov 8, 2026.

This range next to 2 other live CNA roles with the nearest advertised base floor
Chart as a table
This range next to 2 other live CNA roles with the nearest advertised base floor
RolePublished base
VP, Regional Underwriting Manager Midwest (Core Middle Market) (this listing)$194K - $308K
VP, National Distribution Leader$194K - $308K
AVP, Claims Recovery$152K - $242K

Same $100K to $400K scale as every card. All CNA roles · How to read the bar

Observed changes

  1. First observed on the employer's board
  2. Began meeting the published-salary criteria
Observed since
Employer-stated posting date
2026-07-15
Where this pay comes from

Location as the employer wrote it: Chicago, IL, USA

t of Columbia, California, Colorado, Connecticut, Illinois, Maryland, Massachusetts, New York and Washington, the national base pay range for this job level is $194,000 to $308,000 annually. Salary determinations are based on various factor

Method
Employer text, read with fixed rules and re-verified
Checked
Rule set
us-base-v2

The pay passage appears in the employer's own job text. Fixed, deterministic rules located it, and the passage below was checked against the stored copy of the posting.

What we verified

  • The pay figures come from the employer's own listing, quoted exactly above.
  • The pay is an annual base salary in US dollars with a minimum of at least $100,000.
  • The role was publicly listed on the employer's job board when last checked.

We do not verify what the employer will actually offer, whether the employer is still recruiting for the role, or anything beyond what the employer published. Full methodology.

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